High Output: The Future of Engineering

I asked Muddassar Shaikh where engineering work is actually heading, and he answered with what he admitted could be the setup to a joke. “This can be the start of a great joke,” he said. “A product manager and a designer and an engineer walk into a room, and then jam on the idea together. And they come out with a working prototype instead of coming out with a spec.” What’s missing is the handoffs....

Twenty minutes into our conversation, I asked Charity Majors how engineering leaders should be finding good junior engineers right now. “God, I don’t fucking know.” She apologized, then doubled back. “Sorry. Excuse me. You do need them. They’re not hard to find.” That answer is the whole interview in miniature. How a junior breaks into engineering today, Charity will tell you, is genuinely unresol...

Superhuman built its reputation on a number: 100 milliseconds. Every interaction in the product has to feel instantaneous. Not fast. Instantaneous. That’s the threshold where the human brain stops perceiving lag and starts feeling like the software is an extension of thought. They’ve been engineering to that constraint for years, and it has shaped everything — the architecture, the hiring bar, the...

We recorded this episode with Steve back in October of 2025, before he invented Beads and Gastown . Several of his predictions have aged well in the months since. Steve Yegge has been VP or head of engineering at four companies. He keeps stepping down on purpose. Not because things went wrong — his organizations were doing well. He’s the kind of leader whose reputation travels through a company; a...

Most engineering leaders spend enormous energy on process. Which agile framework. Which sprint cadence. Which AI coding tool to adopt. How to standardize workflows across teams. The assumption is that the right process produces the right outcomes. Gaurav Gargate has come to believe the opposite. Get the principles right, and the process can flex. Gaurav is VP of Engineering at Confluent, where he...

Some engineering teams are seeing real, measurable AI productivity gains. Cursor is transforming how frontend developers build React apps. AI-assisted code review is catching bugs before deployment. Prototypes that took weeks now take days. But not everyone’s seeing the same results. Raju Matta runs engineering for Cambridge Mobile Telematics —200+ engineers, three countries, petabytes of real-tim...

When you’ve bootstrapped an engineering org from 2 people to 500, working with Fortune 500 clients like Intel and Samsung, you learn something most AI builders miss: the best technology doesn’t always ship. Muhammad Atif , President and CTO of PureLogics , recently deployed an on-prem AI model that hits 70% of the accuracy of their original cloud-based prototype. That 30% accuracy gap represents t...

When you provision thousands of GPU clusters weekly for Apple, Spotify, OpenAI, Uber, Runway, and Cursor, you see something nobody else does. From the infrastructure layer, the patterns are unmistakable. Different companies, different products, different use cases—but they’re all hitting the same bottlenecks. Jaikumar Ganesh would know. As Head of Engineering at Anyscale , he runs Ray —the distrib...

Most engineering leaders learn leadership the hard way. They get promoted from IC roles and suddenly find themselves managing people they used to work alongside. They default to command-and-control because that's what they've seen. They struggle with influence across teams they don't control. The transition is messy, stressful, and often unsuccessful. Richard Ford took a different path. He's the V...

Most engineering leaders are still running interviews like it's 2004. Multiple coding rounds. Brain twisters on whiteboards. Engineers throwing their favorite puzzle at candidates. The whole process optimized for showing off interviewer cleverness rather than predicting job performance. Ashwin Baskaran figured this out early. He's the VP of Engineering at Mercury , the fintech that more than 200,0...

Most hypergrowth startups hire fast and regret it later. They compromise on quality to fill seats, rationalize cultural misfits as "learning experiences," and spend months fixing the technical debt created by rushed hires. Adam Kirk took a different approach: he hired 35 engineers in 12 months and raised his quality bar with each hire. Adam is co-founder and CTO of Jump , where they've built a not...

Mike Weaver followed every rule in the engineering playbook. When LLMs started disrupting Replicant's voice automation platform, he did exactly what conventional wisdom dictates: "Let's incorporate it in parts of the product. Let's improve these parts of the experience." Keep the legacy system running, gradually migrate functionality, minimize risk. But months into this approach, Mike hit the wall...

Most engineering leaders think about AI wrong. When they see a new model, they ask: "How fast can we ship this?" But the interesting question is: "Where will this break?" Troy Astorino figured this out early. He's the CTO of PicnicHealth , and they've built something remarkable: an 8 billion parameter model that beats much larger frontier models at medical tasks. Because Troy understood exactly wh...

This week on High Output, Adil Ajmal , CTO of Fandom , tackles the question every engineering leader is wrestling with: How do you get an entire organization to adopt AI without simply mandating it? While many engineering leaders are navigating AI adoption with a mix of top-down encouragement and bottom-up experimentation, Adil took a more structured path. He set a specific, measurable goal: 80% A...

This week on High Output, Tacita Morway, CTO of Textio, reveals why the biggest challenge in the AI era isn't learning new tools—it's learning what not to build. From landscape design to heavy machinery operation to leading engineering teams, Tacita's unconventional path taught her that management isn't about having all the answers. It's about asking better questions. Now, as AI transforms how we...

As AI reshapes the what of engineering, leadership is about focusing on the who . This week on High Output, Glenn Veil, SVP of Engineering at Order.co , shares how three decades of unplanned leadership taught him the most important lesson of all: technology will always evolve—but people remain the constant. Glenn didn't start out aiming to lead. One sudden promotion, a broken website, and a confus...

We’re thrilled to share something we’ve been working on at Maestro AI behind the scenes: High Output , a weekly conversation series where visionary engineering leaders unpack how they’re shipping faster, scaling smarter, and future-proofing their teams. These are unfiltered, from-the-trenches takes on running engineering teams amidst seismic transformations in the tech industry. 🌌 Why these conve...